Azo dyestuff.



KURT IDESAlii'hRI, 033 COLOGNE, GERI-L'ANY,

8'35 NEW YORK, N. 31"., A

CORPGRATION OF NE'iI A DYESTUFF.

No Drawing.

(R meaning an giryl e. g.

2Q -ct-H=-.--o5r1 can be obtained by combining a diazo compound of anortho-nitranilin, e. g. orthonitraniiiin nitro-toluidin ((1H,, N0 NFL,-1: 3:4), chloro-nitranilin (Cl N0 NI-1 4: :2 It) withaceto-acetic-anilid-pera-carboxylic acid.

The new dyes are in the shape of their alkaline salts yellowish powderssoluble in Water and in concentrated sulfuric acid generally With. ayellowish coloration; they are particularly suitable for the productionof color ls es which are distinguished by their pure greenish-yellowshades and excellent iastness to oil and to Water. Upon treatment withstannous chloricl and hydrochloric acid they are reduced, so orthodiamin of the benzene series being obtained. Theeceto-acetic-anilid-pal-mos ooxylic acid 46 can be obtained by heating apara-aminobenzoic acid ester with acct-o acetic ester Application filedApril 1,

uceto acetic anilid -para and of the new ecetoecctiou 1 lioXlyic-ecid,the parts being by weight:

Example 1: 165 parts of pare--11 .illlOrlflfiPr zo1c-etliyl-ester aredissolved in 57:3 ports oi solvent naphtha and 150 partsscetoacetic-ether are allowed to run gradually into the boilingsolution. the con".ai;iing it being connected with E1 downward directedcondenser. When the reaction is complete the new ester crystallizes fromconcentrated solution with an. lznos't (marititative yield. It issoluble in the semi organic solvents zindmelts :11'3'125" (3. 2 1-9parts of the ester thus obtained are Well mixed with 100 parts ofalcohol and 21 hot solution of 125 parts of caustic soda in 400 parts ofWater is gradually added "to o alcoholic paste in such-manner that thetermperature of the mixture is about C. After stirring for half H11 hourat ternpera'ture the ester is completely dissolved and the newaceto-ece'tic-anili l-pera-csrboxylic acid is precipitated from thesolution by addition of H l. composition at 185 In order to illustratethe process for the production of the new 1120 dyes the followingexample is given, the parts being by weight:

Example 2: 152 parts of S-nitro--toluidin:

cm I l -uofl me are dissolved by heating in 200 parts of concentratedsulfuric acid. The solution is poured on ice; the finely dividedprecipitate which separates is filtered oii, made into a paste with 300parts of crude h nlrochloric acid and diazotized at 5 G. with 69 partsof sodium nitrit. The mineral acid of the diozo solution is almostcompletely neutralized at the same temperature With sodium loicerbonnteand the diazo compound is then al- It melts with alelowed to run into sneutral solution of of aceto-acetic-ecid-enilid-pare-csr boxylic acid towhich 150 parts of sodium bicarbonate has been added.

The sodium salt of the new color is a yellowish powder having in a freestate most probably the formula:

soluble in Water with a yellowish coloration. It can be converted, bythe usual methods suitable for the preparation of lakes, into the colorlakes, for instance into the barium or calcium lake. Upon treatment withstannous clilorid and hydrochloric acid diaminomethylbcnzene isobtained.

I claim 1. The new dyestulis derivable from a diazotizedortho-nitranilin" and aceto-aceticacid-anilid-para-carboxylic-acidhaving in a free state most probably the formula:

(Rmeaning aryl) which are in the shape of their alkaline salts yellowishpowders soluble OOH The new dyestu'ff derivable from di azotized3-nitro-4-toluidin and aceto-aceticacid-anilid-para-carboxylic acidhaving in a free state most probably the formula:

which is in the shape of its yellowish powder soluble in'water with ayellowish coloration; yieldin upon reduction with stannous chlorid andhydrochloric acid diaminometh lbenzene; and yielding greenish-yellowcolor lakes, substantially as described.

In testimony my hand in the w1tnesses.

whereof I have hereunto set presence of two subscribing KURT 'DESAMARI.

M Witnesses: LOUIS VANDOBI,

HANs Bniicxmm.

alkaline salt a

